EP1086951A1 - Indolverbindungen, ihre Verwendung zum Färben und Schminken von Keratinfasern, sie enthaltende Zusammensetzungen und Färbeverfanren - Google Patents

Indolverbindungen, ihre Verwendung zum Färben und Schminken von Keratinfasern, sie enthaltende Zusammensetzungen und Färbeverfanren Download PDF

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Publication number
EP1086951A1
EP1086951A1 EP00402372A EP00402372A EP1086951A1 EP 1086951 A1 EP1086951 A1 EP 1086951A1 EP 00402372 A EP00402372 A EP 00402372A EP 00402372 A EP00402372 A EP 00402372A EP 1086951 A1 EP1086951 A1 EP 1086951A1
Authority
EP
European Patent Office
Prior art keywords
formula
composition
dyeing
fibers
keratin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP00402372A
Other languages
English (en)
French (fr)
Other versions
EP1086951B1 (de
Inventor
Nicole Bonaventure
Patrick Gillard
Gilles Barre
Michel Dubois
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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Filing date
Publication date
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1086951A1 publication Critical patent/EP1086951A1/de
Application granted granted Critical
Publication of EP1086951B1 publication Critical patent/EP1086951B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes

Definitions

  • the subject of the invention is new indole compounds, their use as of direct dyes in compositions intended for dyeing materials keratin and in particular compositions intended for dyeing fibers human keratin and in particular of the hair, and in compositions cosmetics intended for making up the skin, nails and lips, dyeing or makeup compositions containing them and the dyeing process direct correspondent.
  • new indole compounds of formula (I) below defined in the range of orange to red shades, which are suitable for use as a direct dye in dyeing.
  • These new dyes also make it possible to obtain orange to red shades, powerful, having excellent properties of resistance to the various treatments which the keratin fibers can undergo, and in particular the hair, with respect to light, washes, permanent waving and sweating.
  • the alkyl radical may be linear or branched and in particular denotes for example a methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, ter.-butyl radical; the C 1 -C 4 monohydroxyalkyl radical more particularly denotes the radical -CH 2 -CH 2 OH and the polyhydroxyalkyl radical C 1 -C 4 more particularly denotes the radical -CHOH-CH 2 OH.
  • the indole compounds of formula (I) can be obtained by oxidation of the corresponding indole in a solvent medium according to oxidation methods generally well known to those skilled in the art.
  • an alcoholic medium methanol, ethanol, n-propanol, isopropanol, n-butanol, terbutanol
  • the invention also relates to a process for the preparation of an indole compound of formula (I), by oxidation in alcoholic medium of a compound of formula (III) described above, in the presence of sodium metaperiodate, and at temperature ambient.
  • a subject of the invention is also the use of the indole compounds of formula (I) described above, as direct dyes in, or for the manufacture of, dyeing or makeup compositions for materials keratin, and in particular for human keratin fibers such as hair.
  • the subject of the invention is also a composition for dyeing or making up keratin materials, characterized in that it comprises, in a medium suitable for dyeing or makeup, an effective amount of at least one compound of formula (I) according to the invention.
  • the term “materials” is mainly understood keratin, facial or body skin, lips, nails, fibers human keratin such as human hair, body hair, eyelashes, eyebrows, and also keratin fibers such as natural textile fibers including especially wool.
  • the subject of the invention is in particular a composition for direct dyeing of human keratin fibers such as the hair, characterized in that it includes, in a medium suitable for dyeing, an effective amount of at least at least one compound of formula (I) according to the invention.
  • the compound or compounds of formula (I) in accordance with the invention preferably represent from 0.05 to 10% by weight approximately of the total weight of the dye composition, and even more preferably from 0 0.05 to 0.5% by weight approximately of this weight.
  • the compound or compounds of formula (I) in accordance with the invention preferably represent from 0.05 to 20% by weight approximately of the total weight of the composition, and even more preferably from 0.05 at about 5% by weight of this weight.
  • the compounds of formula (I) in accordance with the invention can also be used, in the well-known processes for the oxidation dyeing of keratin fibers human, using oxidation dyes (dye precursors oxidation and possibly couplers), to nuance or enhance the reflections dyes obtained with oxidation dyes.
  • oxidation dyes die precursors oxidation and possibly couplers
  • the dye composition according to the invention may also contain, to widen the palette of shades and obtain various shades, in addition to the orange compounds to red of formula (I) according to the invention, other conventional direct dyes used, and in particular, benzene nitro dyes, such as nitrophenylenediamines, nitrodiphenylamines, nitroanilines, ethers of nitrated phenol or nitrophenols, nitropyridines, dyes anthraquinonics, mono- or di-azo dyes, triarylmethanics, azine, acridinic and xanthenic, or metalliferous dyes.
  • benzene nitro dyes such as nitrophenylenediamines, nitrodiphenylamines, nitroanilines, ethers of nitrated phenol or nitrophenols, nitropyridines, dyes anthraquinonics, mono- or di-azo dyes, triarylmethanics, azine, acridin
  • the proportion of all these other direct addition dyes can vary between 0.5 and 10% by weight approximately relative to the total weight of the dye composition.
  • the medium suitable for dyeing generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds which are not sufficiently soluble in water.
  • organic solvent mention may, for example, be made of lower C 1 -C 4 alkanols, such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, propylene glycol monomethyl ether, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof. It can also contain fatty substances such as oils and waxes.
  • the solvents can be present in proportions preferably included between 1 and 70% by weight approximately relative to the total weight of the composition dye, and even more preferably between 5 and 40% by weight approximately.
  • composition according to the invention fatty amides such as mono- and di-ethanolamides of acids derived from coconut, lauric acid or oleic acid, at concentrations of between approximately 0.05 and 10% by weight. It is also possible to add to the composition according to the invention surfactants well known from the prior art and of anionic, cationic, nonionic, amphoteric, zwitterionic type or their mixtures, preferably in a proportion of between about 0.1 and 50% by weight and advantageously between about 1 and 20% by weight relative to the total weight of the composition. Thickening agents can also be used in an amount ranging from about 0.2 to 5%.
  • Said dye composition may also contain various usual adjuvants such as antioxidants, perfumes, sequestering agents, dispersing agents, hair conditioning agents, preserving agents, opacifying agents, as well as any other adjuvant. usually used in dyeing keratin materials.
  • the pH of the dye composition according to the invention intended for dyeing keratin fibers is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value using acidifying or basifying agents usually used in fiber dyeing keratinous.
  • acidifying agents there may be mentioned, by way of example, mineral acids or organic like hydrochloric acid, orthophosphoric acid, acid sulfuric, carboxylic acids like acetic acid, tartaric acid, citric acid, lactic acid, sulfonic acids.
  • basifying agents there may be mentioned, by way of example, ammonia, alkali carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and compounds of formula (IV) below: in which W is a propylene residue optionally substituted by a hydroxyl group or a C 1 -C 6 alkyl radical; R 6, R 7, R 8 and R 9, identical or different, represent a hydrogen atom, an alkyl radical C 1 -C 6 alkyl or hydroxy C 1 -C 6.
  • the dye composition according to the invention can be in forms various, such as liquids, creams, gels, poultices, or in any other form suitable for dyeing materials keratin, and in particular human hair.
  • it can be pressurized in aerosol can in the presence of a propellant and form a foam.
  • the cosmetic compositions intended for make-up are in particular makeup products for the face or lips such as eyeshadows or cheek, powders and blushes, foundations, sticks or lip lacquers and make-up products for the human body; they are also products of makeup of eyelashes, eyebrows and nails, such as mascaras, pencils for eyebrows, the liner also called “eyeliner” and nail polish.
  • Another subject of the invention relates to a process for dyeing keratin fibers and in particular human keratin fibers such as the hair, by direct dyeing, consisting in letting a composition containing at least one compound of formula (I) according to l invention for dry or wet keratin fibers.
  • the composition according to the invention can be used as a leave-in composition, that is to say that after application of the composition to the fibers, it is dried without intermediate rinsing.
  • after application of the composition to the fibers for an exposure time varying between 3 and 60 minutes approximately, preferably between 5 and 45 minutes approximately, it is rinsed, optionally washed, then rinsed again , and we dry.
  • the following direct hair dye composition was prepared: Compound of formula (II) 10 -3 mole 0.6g Benzyl alcohol 14 g Ethanol 46g Demineralized water qs 100g
  • composition was applied to locks of natural gray hair or permed to 90% whites at a rate of 5 g of composition per gram of hair and left on for 30 minutes. After rinsing with running water and drying, the hair was dyed in a deep red shade.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)
  • Indole Compounds (AREA)
EP00402372A 1999-09-22 2000-08-28 Indolverbindungen, ihre Verwendung zum Färben und Schminken von Keratinfasern, sie enthaltende Zusammensetzungen und Färbeverfanren Expired - Lifetime EP1086951B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9911833 1999-09-22
FR9911833A FR2798931B1 (fr) 1999-09-22 1999-09-22 Nouveaux composes indoliques, leur utilisation pour la teinture et le maquillage des matieres keratiniques, compositions les contenant et procedes de teinture

Publications (2)

Publication Number Publication Date
EP1086951A1 true EP1086951A1 (de) 2001-03-28
EP1086951B1 EP1086951B1 (de) 2002-06-26

Family

ID=9550116

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00402372A Expired - Lifetime EP1086951B1 (de) 1999-09-22 2000-08-28 Indolverbindungen, ihre Verwendung zum Färben und Schminken von Keratinfasern, sie enthaltende Zusammensetzungen und Färbeverfanren

Country Status (6)

Country Link
US (2) US6407260B1 (de)
EP (1) EP1086951B1 (de)
AT (1) ATE219775T1 (de)
DE (1) DE60000234T2 (de)
ES (1) ES2179009T3 (de)
FR (1) FR2798931B1 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6407260B1 (en) * 1999-09-22 2002-06-18 L'ORéAL S.A. Indole compound

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050278871A1 (en) * 2003-11-05 2005-12-22 Luc Gourlaouen Compositions comprising at least one compound chosen from heptafulvene and tropolone derivatives, and dyeing process thereof
US7582121B2 (en) 2005-05-31 2009-09-01 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one heterocyclic direct dye
US7485156B2 (en) 2005-05-31 2009-02-03 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler and at least one associative polyurethane polymer
US7488356B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising at least one diamino-N,N-dihydropyrazolone derivative, at least one coupler, and at least one surfactant
US7488355B2 (en) 2005-05-31 2009-02-10 L'oreal S.A. Composition for dyeing keratin fibers, comprising a diamino-N,N-dihydropyrazolone compound, a coupler, and a polyol
FR2886132B1 (fr) 2005-05-31 2007-07-20 Oreal Composition pour la teinture des fibres keratiniques comprenant un derive de diamino-n,n-dihydro-pyrazolone, un coupleur et un colorant direct heterocyclique

Citations (2)

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Publication number Priority date Publication date Assignee Title
FR2618069A1 (fr) * 1987-07-17 1989-01-20 Oreal Poudre minerale ultrafine comportant des pigments melaniques, son procede de preparation et son utilisation en cosmetique
FR2677544A1 (fr) * 1991-06-14 1992-12-18 Oreal Composition cosmetique contenant un melange de nanopigments d'oxydes metalliques et de pigments melaniques.

Family Cites Families (14)

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LU87256A1 (fr) * 1988-06-21 1990-02-28 Oreal Procedes de teinture de fibres keratiniques a base de 5,6-dihydroxyindole et d'au moins un sel de terre rare et compositions de mise en oeuvre
US4964754A (en) * 1989-05-24 1990-10-23 Garner James D Concrete screeding machine
US5752982A (en) * 1991-03-28 1998-05-19 L'oreal Methods for dyeing keratinous fibers with compositions which contain aminoindole couplers, oxidation dye precursors, and oxidizing agents at acid pHs
US5938792A (en) * 1991-04-18 1999-08-17 L'oreal Process for dyeing keratinous fibers with aminoindoles and oxidation dye precursors at basic Ph's and dyeing agents
US5468872A (en) * 1993-09-16 1995-11-21 Cephalon, Inc. K-252a functional derivatives potentiate neurotrophin-3 for the treatment of neurological disorders
FR2722686B1 (fr) * 1994-07-22 1996-08-30 Oreal Set, procede, dispositif et composition de teinture des fibres keratiniques
FR2736640B1 (fr) * 1995-07-13 1997-08-22 Oreal Compositions de teinture des fibres keratiniques contenant des derives n-substitues du 4-hydroxy indole, nouveaux derives, leur procede de synthese, leur utilisation pour la teinture, et procede de teinture
FR2742047B1 (fr) * 1995-12-06 1998-01-16 Oreal Compositions de teinture des fibres keratiniques contenant des derives n-substitues de la 4-hydroxy indoline, nouveaux derives, leur procede de synthese, leur utilisation pour la teinture, et procede de teinture
US5616724A (en) * 1996-02-21 1997-04-01 Cephalon, Inc. Fused pyrrolo[2,3-c]carbazole-6-ones
FR2748274B1 (fr) * 1996-05-03 1998-06-12 Oreal Nouveaux diamino pyrazoles, leur synthese, compositions de teinture des fibres keratiniques les contenant, procede de teinture des fibres keratiniques
FR2750048B1 (fr) * 1996-06-21 1998-08-14 Oreal Compositions de teinture des fibres keratiniques contenant des derives pyrazolo-(1, 5-a)-pyrimidine, procede de teinture, nouveaux derives pyrazolo-(1, 5-a)-pyrimidine et leur procede de preparation
US6309426B1 (en) * 1996-12-23 2001-10-30 The Procter & Gamble Company Hair coloring compositions
FR2760012B1 (fr) * 1997-02-26 2000-08-18 Oreal Compositions pour la teinture des fibres keratiniques contenant des para-aminophenols, procede de teinture, nouveaux para-aminophenols et leur procede de prepraration
FR2798931B1 (fr) * 1999-09-22 2001-11-16 Oreal Nouveaux composes indoliques, leur utilisation pour la teinture et le maquillage des matieres keratiniques, compositions les contenant et procedes de teinture

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2618069A1 (fr) * 1987-07-17 1989-01-20 Oreal Poudre minerale ultrafine comportant des pigments melaniques, son procede de preparation et son utilisation en cosmetique
FR2677544A1 (fr) * 1991-06-14 1992-12-18 Oreal Composition cosmetique contenant un melange de nanopigments d'oxydes metalliques et de pigments melaniques.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
P. MANINI ET AL: "Acid-promoted competing pathways in the oxidative polymerization of 5,6-dihydroxyindoles and related compounds: straightforward cyclotrimerization routes to diindolocarbazole derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 63, 1998, EASTON US, pages 7002 - 7008, XP002138534 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6407260B1 (en) * 1999-09-22 2002-06-18 L'ORéAL S.A. Indole compound
US6692538B2 (en) 1999-09-22 2004-02-17 L'ORéAL S.A. Use of novel indole compounds for dyeing and making up keratin materials, compositions comprising them and dyeing processes

Also Published As

Publication number Publication date
US6692538B2 (en) 2004-02-17
ATE219775T1 (de) 2002-07-15
FR2798931B1 (fr) 2001-11-16
US20020165401A1 (en) 2002-11-07
FR2798931A1 (fr) 2001-03-30
EP1086951B1 (de) 2002-06-26
US6407260B1 (en) 2002-06-18
DE60000234D1 (de) 2002-08-01
ES2179009T3 (es) 2003-01-16
DE60000234T2 (de) 2002-10-24
US20030187277A9 (en) 2003-10-02

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